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Chemical Structure| 26260-02-6 Chemical Structure| 26260-02-6
Chemical Structure| 26260-02-6

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Synonyms: o-Iodobenzaldehyde

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Product Details of 2-Iodobenzaldehyde

CAS No. :26260-02-6
Formula : C7H5IO
M.W : 232.02
SMILES Code : O=CC1=CC=CC=C1I
Synonyms :
o-Iodobenzaldehyde
MDL No. :MFCD00039570
InChI Key :WWKKTHALZAYYAI-UHFFFAOYSA-N
Pubchem ID :643439

Safety of 2-Iodobenzaldehyde

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 2-Iodobenzaldehyde

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 26260-02-6 ]

[ 26260-02-6 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 26260-02-6 ]
  • [ 62327-21-3 ]
  • [ 403705-03-3 ]
  • 2
  • [ 26260-02-6 ]
  • [ 53903-49-4 ]
  • [1-(2-Iodo-phenyl)-meth-(E)-ylidene]-(4-methoxy-2-trifluoromethyl-phenyl)-amine [ No CAS ]
  • 3
  • [ 26260-02-6 ]
  • [ 262373-15-9 ]
  • [ 2840-51-9 ]
  • [ 1705-89-1 ]
  • 4
  • [ 26260-02-6 ]
  • [ 252054-88-9 ]
  • [ 479-79-8 ]
  • 5
  • [ 26260-02-6 ]
  • [ 536-74-3 ]
  • [ 59046-72-9 ]
YieldReaction ConditionsOperation in experiment
92% With triethylamine; In water; at 20℃; for 8h; General procedure: An aryl halide (1.0 mmol) and a terminal alkyne (1.2 mmol) were added to a mixture of PS-tsu-Pd(II) complex (3) (0.001 mmol), triethylamine (2.0 mmol), and water (3 mL) in a round bottom flask under vigorous stirring. The mixture was stirred at room temperature for 8 h under aerobic conditions. After completion of the reaction, the mixture was filtered to recover the catalyst. The polymer was washed with water, acetonitrile and subjected to vacuum drying for the next run. Further, the reaction mixture was extracted with ethyl acetate and dried over MgSO4. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel using ethyl acetate/hexane as the eluent to give the corresponding coupling products.
66% With cetyltrimethylammonim bromide; potassium carbonate; In water; at 110℃; for 10h; General procedure: In a typical reaction, a mixture of aryl halides (1.2 mmol), phenylacetylene (1.5 mmol), K2CO3 (276 mg, 2 mmol), cetyltrimethylammonium bromide (36 mg, 0.1 mmol), H2O (3 mL) and catalyst 3 (30 mg, 0.03 mmol of Cu) was stirred at 110 C for 10 h, then cooled to room temperature, filtered and washed with ethyl acetate (3 × 10 mL). The combined organic layers were extracted with water, saturated brine solution, and dried over anhydrous Na2SO4. The organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography by using ethyl acetate/hexane (1:9) as eluent to give the corresponding product. All the products were confirmed by 1H, 13C NMR, and mass spectroscopic analysis. See the Supporting Information for full details.
  • 7
  • [ 26260-02-6 ]
  • [ 38980-96-0 ]
  • [ 1208259-10-2 ]
  • 8
  • [ 26260-02-6 ]
  • [ 57297-29-7 ]
  • [ 1208259-27-1 ]
  • 9
  • [ 118-48-9 ]
  • [ 26260-02-6 ]
  • [ 658-27-5 ]
  • [ 1370643-36-9 ]
  • 10
  • [ 26260-02-6 ]
  • [ 10328-92-4 ]
  • [ 658-27-5 ]
  • [ 1370643-42-7 ]
  • 11
  • [ 26260-02-6 ]
  • [ 1173707-01-1 ]
  • [ 109-77-3 ]
  • 10-fluoroindolo[1,2-a]quinazoline-7-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% General procedure: A dry sealed tube was charged with a magnetic stirrer, substitutedN-(2-iodophenyl)acetamide (100 mg for each example,0.38 mmol), malononitrile or 2-sulfonylacetonitriles(0.46 mmol, 1.2 equiv), CuI (0.038 mmol, 0.1 equiv), L-proline(0.076 mmol, 0.2 equiv), and K2CO3 (0.76 mmol, 2 equiv) in0.77 mL of DMSO. The tube was evacuated and backfilled withargon and the process was repeated three times. The mixturewas stirred at 80 °C for 12 h under an argon atmosphere.After the starting material was consumed completely,2-iodobenzaldehyde (0.4 mmol, 1.05 equiv) with 0.77 mL ofDMSO was charged successively to the tube via syringe,and then the resulting mixture was stirred at 80 °C foranother 12 h under an argon atmosphere. After thereaction was complete, the reaction mixture was cooledto room temperature and the reaction mixture was partitionedbetween ethyl acetate or dichloromethane and water. Theorganic layer was separated and the aqueous layer was extractedwith ethyl acetate or dichloromethane for three times. Thecombined organic solution was washed with water, brine, driedover anhydrous Na2SO4, and concentrated under reducedpressure to give the crude product. Purification by chromatographyon silica gel using petroleum ether/ethyl acetate ordichloromethane/ethyl acetate as eluent provided the desiredproduct.
  • 12
  • [ 26260-02-6 ]
  • [ 19591-17-4 ]
  • [ 109-77-3 ]
  • indolo[1,2-a]quinazoline-7-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% A dry sealedtube was charged with a magnetic stirrer, substituted <strong>[19591-17-4]N-(2-iodophenyl)acetamide</strong>(100 mg for each example, 0.38 mmol ), malononitrile or2-sulfonylacetonitriles(0.46 mmol, 1.2 equiv), CuI (0.038mmol, 0.1equiv),L-proline (0.076 mmol, 0.2 equiv), and K2CO3(0.76 mmol, 2 equiv) in 0.77 mL of DMSO. The tube wasevacuated and backfilled with argon and the process was repeated three times.The mixture was stirred at 80 C for 12 h under a argonatmosphere. After thestarting material was consumed completely, 2-iodobenzaldehyde (0.4 mmol, 1.05equiv) with 0.77 mL of DMSO was charged successively to the tube via syringe,and then the resulting mixture was stirred at 80 C for another 12 h underanargonatmosphere. After the reaction was complete, the reaction mixture wascooled to room temperature, the reaction mixture was partitioned between ethylacetate or dichloromethane and water. Organic layer was separated, and aqueouslayer was extracted with ethyl acetate or dichloromethane for three times, thecombined organic solution was washed with water, brine, dried over anhydrous Na2SO4, and concentrated under vacuum togive crude product. The crude product was purified by chromatography on silicagel (Petroleum ether/EtOAc = 4:1 as eluent) to give 4a. Yellow solid(67mg, 72%), mp 219-220 C; 1H NMR (500 MHz,[D6]DMSO) δ9.12 (s, 1H), 8.70 (d, J = 8.0 Hz, 1H), 8.62 (s, 1H),8.17 (d, J = 7.5 Hz, 1H), 8.01 (t, J = 7.4 Hz, 1H), 7.83 (s, 1H),7.64 (t, J = 7.5 Hz, 1H), 7.54 (d, J = 3.0 Hz, 2H); 13C NMR (126 MHz, [D6]DMSO) δ156.56, 146.69, 136.15,135.59, 130.44, 129.07, 127.41, 125.33, 124.54, 124.50, 119.05, 118.77, 115.66,115.63, 115.14, 78.23; MS (ESI, m/z) 244 [M+H]+; HRMS (ESI): calcd.for C16H9N3Na [M+Na]+ 266.0694, found 266.0696.
  • 13
  • [ 26260-02-6 ]
  • [ 19591-17-4 ]
  • [ 2274-42-2 ]
  • 7-(methylsulfonyl)indolo[1,2-a]quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% General procedure: A dry sealed tube was charged with a magnetic stirrer, substituted<strong>[19591-17-4]N-(2-iodophenyl)acetamide</strong> (100 mg for each example,0.38 mmol), malononitrile or 2-sulfonylacetonitriles(0.46 mmol, 1.2 equiv), CuI (0.038 mmol, 0.1 equiv), L-proline(0.076 mmol, 0.2 equiv), and K2CO3 (0.76 mmol, 2 equiv) in0.77 mL of DMSO. The tube was evacuated and backfilled withargon and the process was repeated three times. The mixturewas stirred at 80 C for 12 h under an argon atmosphere.After the starting material was consumed completely,2-iodobenzaldehyde (0.4 mmol, 1.05 equiv) with 0.77 mL ofDMSO was charged successively to the tube via syringe,and then the resulting mixture was stirred at 80 C foranother 12 h under an argon atmosphere. After thereaction was complete, the reaction mixture was cooledto room temperature and the reaction mixture was partitionedbetween ethyl acetate or dichloromethane and water. Theorganic layer was separated and the aqueous layer was extractedwith ethyl acetate or dichloromethane for three times. Thecombined organic solution was washed with water, brine, driedover anhydrous Na2SO4, and concentrated under reducedpressure to give the crude product. Purification by chromatographyon silica gel using petroleum ether/ethyl acetate ordichloromethane/ethyl acetate as eluent provided the desiredproduct.
  • 14
  • [ 26260-02-6 ]
  • [ 19591-17-4 ]
  • [ 7605-28-9 ]
  • 7-(phenylsulfonyl)indolo[1,2-a]quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% General procedure: A dry sealed tube was charged with a magnetic stirrer, substituted<strong>[19591-17-4]N-(2-iodophenyl)acetamide</strong> (100 mg for each example,0.38 mmol), malononitrile or 2-sulfonylacetonitriles(0.46 mmol, 1.2 equiv), CuI (0.038 mmol, 0.1 equiv), L-proline(0.076 mmol, 0.2 equiv), and K2CO3 (0.76 mmol, 2 equiv) in0.77 mL of DMSO. The tube was evacuated and backfilled withargon and the process was repeated three times. The mixturewas stirred at 80 C for 12 h under an argon atmosphere.After the starting material was consumed completely,2-iodobenzaldehyde (0.4 mmol, 1.05 equiv) with 0.77 mL ofDMSO was charged successively to the tube via syringe,and then the resulting mixture was stirred at 80 C foranother 12 h under an argon atmosphere. After thereaction was complete, the reaction mixture was cooledto room temperature and the reaction mixture was partitionedbetween ethyl acetate or dichloromethane and water. Theorganic layer was separated and the aqueous layer was extractedwith ethyl acetate or dichloromethane for three times. Thecombined organic solution was washed with water, brine, driedover anhydrous Na2SO4, and concentrated under reducedpressure to give the crude product. Purification by chromatographyon silica gel using petroleum ether/ethyl acetate ordichloromethane/ethyl acetate as eluent provided the desiredproduct.
  • 15
  • [ 1118-66-7 ]
  • [ 26260-02-6 ]
  • [ 14208-35-6 ]
  • 16
  • [ 26260-02-6 ]
  • [ 1986-47-6 ]
  • (1S*,2R*)-N-(2-iodobenzyl)-2-phenylcyclopropan-1-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
15% General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound.
  • 17
  • [ 26260-02-6 ]
  • [ 16155-03-6 ]
  • 2-(2-iodobenzyl)-4-methyl-1-(4-nitrophenyl)piperazine [ No CAS ]
 

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Technical Information

• Alkyl Halide Occurrence • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Fischer Indole Synthesis • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Julia-Kocienski Olefination • Kinetics of Alkyl Halides • Knoevenagel Condensation • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Dihalides • Reformatsky Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Stetter Reaction • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

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